Trans in the City’s Bobbi Pickard on surviving against the odds: ‘Why am I still here? I don’t know’

Bobbi Pickard attends The PinkNews Awards 2022 at Church House, Westminster, on October 19, 2022

The first time Bobbi Pickard tried to transition, she lost her career overnight.

What followed was a turbulent few years. In her darkest hour, she attempted suicide, believing she no longer had a future.

“When I first tried to medically transition in the early 2000s, it cost me my career. It was professional suicide, basically,” Bobbi Pickard tells PinkNews.

Pickard ultimately became self-employed, a move which pushed her medical transition back by a decade. It was during that period of her life that she attempted suicide.

Thankfully, Bobbi survived. Today she’s the proud CEO of Trans in the City, a collaborative project that works to raise awareness for trans and non-binary people in business globally. Trans in the City has recently partnered with PinkNews to “bring the truth of what it means to be trans and non-binary” to businesses and to society, Pickard explains.

“What we’re here for is to promote those trans and non-binary people that are doing such amazing things in our society,” she says.

“We’ve got helicopter rescue pilots, we’ve got rocket scientists working at NASA, we’ve got paramedics and nurses and members of the armed forces. None of their stories are getting out there and they’re doing such amazing things for society day in, day out.

“That’s why Trans in the City is here – to try and promote the positive things that trans and non-binary people are doing for our society.”

Bobbi Pickard wants to end transphobia in the workplace

Trans in the City came about after Bobbi Pickard finally came out in the business world and medically transitioned in 2016. She quickly started to see the gap that was opening up in workplaces – organisations that had trans role models or a budget for diversity training were creating safe spaces for trans employees, but those with less money and fewer trans people weren’t.

In 2017, Pickard got a few organisations together and ran “a really quiet event” during Trans Awareness Week.

“It was a raging success so I ran a slightly bigger one the year after,” she says.

Bobbi Pickard pictured in a selfie.

Bobbi Pickard. (Supplied)

“The first proper year of Trans in the City, we had five organisations join us. The year after we had 64, then we had 250. This year we’ve got the largest venue in Canary Wharf that we’re renting out for the whole day… it’s going to be 600 people going, we’ve now got over 360 organisations all around the world [signed up].”

Today, Pickard and her fellow Trans in the City directors run awareness courses in “every country and definitely every continent – apart from Antartica,” Pickard laughs.

Over time, Trans in the City has turned into a “movement”, she says. It’s all about collaboration – it now has a board of directors that bring a wealth of talent and expertise.

The success of Trans in the City shows that things are changing – but there’s still a lot more work to be done to make workplaces truly inclusive.

“They’re certainly better in bigger global corporates, depending on the country you’re in, obviously,” Pickard says.

Trans in the City CEO Bobbi Pickard pictured against a white background.

Bobbi Pickard is CEO of Trans in the City. (Denis Robinson)

“I think for small and medium sized enterprises, I don’t think things are that much better. Certainly for trans and non-binary people looking for new roles, we still have those challenges. We still see that trans and non-binary people are four times more likely to be unemployed than any other diversity, and we still see those micro-aggressions.

“Sometimes we just see straightforward aggression and abuse in the workplace, and that all stems from a lack of awareness.”

It’d be nice to see the government taking a more open and actually a more up-to-date view of inclusion.

Pickard acknowledges that there will always be a small number of people who “hate for hate’s sake”, but more often than not, she believes transphobia and bigotry is borne out of “a lack of knowledge and a lack of understanding”.

“That’s what we see in the workplace because the workplace is just a reflection of society, so we see that lack of understanding and that lack of acceptance,” she says.

Pickard often receives messages from trans and non-binary people who say their lives are “hell” – they recount experiences of “constant misgendering” and cruel comments about their appearance and identity.

That bigotry isn’t just about a lack of understanding – it’s also down to misinformation and fear-mongering from some arms of the media and government.

Trans and non-binary people “are doing vital work for our society” in their own industries, Pickard says – but the government only appears to be interested in demonising the community.

“While business becomes more and more inclusive, it seems as though the government wants to go on a different track, and I guess that’s one of the things that really needs to be resolved.

“Business owners are now streaking years ahead of the government’s position. It’d be nice to see the government taking a more open and actually a more up-to-date view of inclusion and bringing itself more in line with the business community.”

Trans people are ‘worth something’

That’s a particularly pertinent point with Trans Day of Remembrance on the horizon. On 20 November, the world will remember those who have died as a result of transphobia.

As Trans Day of Remembrance approaches, Bobbi Pickard wants to show the world that trans people are “worth something”.

“I think the only reason I’m on this side and able to talk about Trans Day of Remembrance and not on the other side and have someone talk about me is a fluke, actually. Simply down to a fluke,” Pickard says.

“I am resilient. I’m a right resilient old bag, and when I decide I want to do something then I will do it hell or high water.”

And I guess, in a few cases, once I got over those bumps of incredibly low times, I really wanted to show people that I wasn’t down and out, that I was worth something.”

“While I am still here, I’m going to make sure that the situation for trans and non-binary people is better.

She continues: “Nine out of 10 trans and non-binary people have suicidal ideation, not because they’re trans but because their life has been made so bleak and hopeless that they just don’t want to be here.

“And honestly, why am I still here? I don’t know. Honestly a couple of times it just literally came down to seconds.”

Bobbi Pickard accepts the LGBTQ CHAMPION award during the Rainbow Honours 2019 at Madame Tussauds.

Bobbi Pickard accepts the LGBTQ CHAMPION award during the Rainbow Honours 2019 at Madame Tussauds. (Stuart C. Wilson/Getty)

Bobbi Pickard doesn’t expect transphobia to be solved during her lifetime, but she hopes she can at least make an impact.

“While I am still here, I’m going to make sure that the situation for trans and non-binary people is better. I won’t be able to solve it – it’s not going to be solved in my lifetime… if I can lay a foundation down for somebody to be able to resolve it then that’s good enough for me.”

Pickard recalls a conversation she had with Stonewall CEO Nancy Kelley, who likened advancing LGBTQ+ rights to carrying a boulder up a hill.

“You can pick that boulder up and you can carry it for a little while but you can’t carry it forever. Sooner or later you’re going to have to put it down and somebody else picks it up,” Pickard says.

“That’s the same for trans and non-binary people’s rights. While I can, I’m going to take that boulder as far as I possibly can, and if I can make things easier for the people that finally get it to the top of the hill and push it down the other side – I won’t be here to see it – but I hope they get a fantastic view when they see it rolling away.”

Suicide is preventable. Readers who are affected by the issues raised in this story are encouraged to contact Samaritans on 116 123 (, or Mind on 0300 123 3393 ( ​Readers in the US are encouraged to contact the National Suicide Prevention Line on 1-800-273-8255.